The Inspirational Life Story of Arlene Dickinson

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Power of Persuasion

When given the unique opportunity to peek behind the scenes and catch a glimpse of a successful entrepreneur and their personal origins, it can be both fascinating and inspiring for those of us who usually only see things from the outside.

Such is the case with Arlene Dickinson, the 55-year-old CEO of Venture Communications and one of the judges on the hit CBC-TV programme Dragons’ Den. The “soft Dragon” as she’s known to many viewers, made a keynote address on The Power of Persuasion in Business at the Metro Toronto Convention Centre for office* Canada where she offered her take on the impact of emerging communications technology as well as her own trials and tribulations along life’s journey.

Dickinson’s life story began on the other side of the world. She was born in South Africa on Oct. 8, 1956 in the small industrial town of Germiston just outside Johannesburg where she lived with her parents and two sisters. Dickinson did not grow up with a great deal of family wealth and privilege as could easily be assumed, given her status today.

A New Homeland

Midway through 1959, Dickinson’s father decided to move the family to Canada where he believed there would be greater opportunities both professionally and in terms of quality of living. Dickinson’s mother, however, did not want to uproot the family and move thousands of kilometres away from what had been their homeland for six generations.

“My mom really did not want to emigrate to Canada,” Dickinson says. “She came because she felt she needed to and had to, but it was done very reluctantly.”

The long trek to Canada included several stops along the way including London, England and it’s a memory Dickinson still has to this day. Specifically, she was standing at the window in their hotel room looking out into the street when her father asked her what she was thinking about.

“I told him I was very excited about going to Canada, as all three-year-olds would say,” Dickinson recounts. “He then kneeled down beside me and said ‘Arlene, I’m going to make you look out the window again and this time I want you to see London. Don’t be so excited about where you’re going that you can’t see where you are.’ The reason this is still in my head all these years later is because I can still see that picture of London because he made me look. And what did he really do? He did what all parents do. He said ‘life is a journey not a destination.’ Make sure that you focus on the moment you’re in, not thinking where you’re headed to the point you don’t enjoy where you are.”

The second memory Dickinson has of her family’s journey from South Africa is landing here in Canada for the very first time. It was a very cold day in February in Montreal, but the final destination would be the even colder Edmonton.

“I always tell Robert Herjavec that our family was two-and-a-half times as wealthy as his because he always tells everybody that his family had $20 in their jeans, but my family actually had $50, so we were really rich compared to him.” If you’ve never seen Dragons’ Den, Herjavec had been a fellow judge alongside Dickinson for five years until his departure from the show at the conclusion of the sixth season. The other current Dragons are: Jim Treliving, Kevin O’Leary, Bruce Croxon and David Chilton, who is the newest addition for season seven, replacing Herjavec.

“When I first met Kevin O’Leary my initial thought was that he’s shorter than I imagined,” Dickinson says with a grin. “But he would tell me he’s a lot taller when he stands on his money.”

Speaking of money, back in the late 1950s you couldn’t take it with you if you were leaving South Africa. Accumulated family wealth was to be left behind. In Germiston, Dickinson’s family was considered middle class. But with only $50 to support five people in Canada, it meant literally starting from scratch.

“We were poor – we were very, very poor,” Dickinson laments. In order to get from Montreal to Edmonton the family purchased a used clunker of a car to get them to their destination. There was an unhappy wife and mother, three young girls and a father driving a barely operational jalopy.

Moving South

After about three years in Edmonton, Dickinson’s father decided it was time to see if Calgary would provide greater opportunities and off they went with all their belongings crammed into the car with them. About half the way between Edmonton and Calgary is a town called Red Deer. It’s a smaller city where people will often stop to rest and eat during the three-hour ride. Dickinson recalls how her mother had knit her and her two sisters matching pink sweaters for the journey south.

Like all kids, the three sisters sat in the back seat fighting most of the way. Dickinson recalls how her dad was getting near his wits-end because of all the fighting and screaming.

“He decides to do what all parents do – bribe us,” Dickinson smiles. “So he stops in Red Deer and gets us strawberry milkshakes. Now I want you to forgive my father for what he does next – because I have.”

As the family continued on with the journey leaving Red Deer, the girls with their milkshakes in hand, wearing those little pink sweaters, they soon began fighting and screaming again after about 10 minutes of silence, which is about the usual amount of time for most kids after being given a bribed treat to keep them quiet.

“My dad finally loses his temper, pulls over to the side of the road, takes the milkshakes and dumps them on our heads,” Dickinson laughs. In fact, she now claims to be the quietest person to be with on a road trip because she learned at a very young age there are consequences for talking in the car.

Making matters worse is that the girls were left like frozen pop tarts during that bitterly cold day and Dickinson’s mother was angry because she’d spent all that time knitting each of the sweaters, which were now covered in strawberry milkshakes. If nothing else, the pink shakes matched the colour of the sweaters.

The family finally made it to Calgary and were driving along McLeod Trail when the car broke down.

“It happened right in front of a car dealership, which sounds fortuitous but really isn’t because there are a million car dealerships on McLeod Trail,” Dickinson chuckles.

From there, her father began to negotiate for another vehicle. The problem was that their broken down wreck was worthless as a trade-in and the family had no money. Left in a dire predicament, Dickinson’s father dejectedly came back and sat inside the broken-down car and told his wife they had to trade in the only thing they had left that was of any value in order to buy another used car.

“My mother looked at him, and as a six-year-old sitting in the back seat I saw what was transpiring,” Dickinson recalls. “What my dad asked my mom to do at that point was to give him her wedding ring.”

This was obviously a very poignant moment in the lives of each family member sitting in the car that day and it’s a memory that will forever be engrained in Dickinson’s mind.

“That wedding ring was more than just a diamond – it was a blue-light diamond that my grandfather, who was a diamond-cutter, had cut for my mother before we left South Africa,” says Dickinson. “So what my dad was asking her to do wasn’t just giving up something that had financial value, what my father was asking her to sacrifice was something that had high emotional value to her and was really the last connection to the country she left and the home she wanted to return to. So as a child I watched my mother take the ring off her finger, tears running down her eyes, and pass it to my father.”

Even at such a young age, Dickinson instinctively knew that while this would help the family survive it was not going to do anything to help keep it together. In fact, she believes it was this very moment in time when she saw the final strings of her parents’ marriage completely dissolve. It was also a day when she witnessed the sacrificial depths people will go in order to survive.

“I saw what a woman or a man will do in order to make sure their family is taken care of and supported,” Dickinson remarks. It’s the tough decision making when no other alternatives are available.

The family purchased another used Pontiac and continued on their way. Dickinson reveals that the dysfunctional aspects of her home life in those early formative years have been extremely influential to her as an adult.

“I think we can take the lives we live and look at them and say the reason I am this way is because I lived in this type of family, and ergo that’s why I am what I am, or we can understand the valuable lessons we learned as children and apply them in a way that’s actually meaningful in our lives.”

Learning from Despair

Despite all those hardships in the early years, Dickinson makes it clear that she loves her parents very much.

“They did the best they could do, but they ended up divorced when I was 13,” she continues. “Through dysfunction we always ended up as a family in some type of drama.”

From that dysfunction, Dickinson became a keen observer – the kid in the family that never wanted to cause any problems or add to the stress of an already tense situation. Taking this approach led to her being able to gauge what people were really trying to say as opposed to what they were saying. She became an accurate observer of human nature and by extension it made her look for the sub text of what was really happening. This observational detail is something that has served Dickinson well in her career as a marketer.

“Later on in life when I became a marketer, what I was really applying was the lessons I’d learned about watching and observing what people really wanted versus what they said they wanted.”

Dickinson’s father was very influential in her life. He was a teacher with a PhD in education who believed in life-long learning. At the age of 16, Dickinson had already graduated grade 12. She accelerated through school with an ability to pass without ever really applying herself. Her father wanted her to attend university but Dickinson decided that was not the route she wanted to take in life.

Angered, her father told her she would end up barefoot and pregnant and always dependent on a man for survival. But Dickinson said her main goal was to do just that – have kids and be married.

“My father was very progressive that way,” she says, regarding his thinking that women had the ability to be strong enough to stand up on their own. “But at 16, I thought I’d work and eventually get married, finding the love of my life and have children. The reason I didn’t want to go to university is because I didn’t think I could pass and didn’t want to put myself in that position. It was my own self-doubt and I convinced myself I wasn’t smart enough to pass in university.”

Starting a Family

At the age of 19, Dickinson did what she set out to do – getting married to her best friend’s brother. By the time she was 27 she had six pregnancies; four children and two miscarriages. Despite having no money, she was happy because she had the family she’d always dreamed about.

“We had to physically build our own home,” Dickinson reveals. “I was hammering nails, painting, helping to lay carpet. How is that relevant to my work today? I was learning the art of managing budgets and people.”

While putting her husband through teacher’s college, one of Dickinson’s first jobs was to collect money on delinquent accounts from her home telephone.

“I learned that sometimes people don’t pay their bills because they’re delinquents and they don’t have any intention of paying – and they never will and they set out to scam or take advantage of somebody. I also learned that sometimes people don’t pay their bills because they can’t; they want to, but they found themselves in a situation where they simply can’t and they really are good people who had every intention of paying.”

Not lost on Dickinson was a very poignant ironic twist. While she was making those calls about delinquent payments to people faced with financial hardships, she and her family were receiving those same types of calls from bill collectors with threats of having the phone or electricity cut off. Many of the essentials needed to survive were on the verge of being shuttered.

Dickinson never believed money had the ability to make her happy, but she also realized that having it could certainly ease off on the stress and tension caused by not being able to pay the household bills that were necessities of life.

Building a Career

Now at the age of 30, Dickinson found herself in a terrible situation: recently divorced, unemployed and having to support four young children. During the divorce proceedings she was informed by the judge that full custody would not be possible with no conceivable means with which to support her children. This was an especially hard pill to swallow, knowing that she had been the one who worked so hard to finance her ex-husband’s education in what resulted in his landing a good teaching position. But here she was left without a job of her own.

It was around this time when Dickinson’s former sister-in-law told her about a job opening at a local television station selling TV time. She got the job and turned out to be very intuitively good at sales.

“I’d learned to listen,” she says. “Sales aren’t about trying to get somebody to buy something they don’t want. It was about being sure I was honest in what I was doing.”

Despite a tremendous amount of success, Dickinson wound up losing the job 18 months later due to cost-cutting measures. During her time at the station, she had worked with a salesman who had since moved on to launch his own company called Venture Communications. Upon hearing of Dickinson’s predicament, he contacted her and made an offer to come in as a partner. Translation: work for free, be partner and hopefully you won’t wind up in too much debt and things might work out in the end.

“I went to Venture and worked for two-and-a-half years without any salary,” Dickinson reveals. “I was hand-to-mouth and living off credit cards. I was doing all the things we tell you not to do on Dragons’ Den.”

During those early lean years, Venture Communications was always on the verge of going out of business at any given moment.

The Big Opportunity

One of company’s first clients was a man named Bob Morrisette, who was in the hair care and hair products industry. He had an idea for a national television advertising programme for hairdressers and hair salons and wanted Venture to go out to Vancouver and make the formal presentation at the Pan-Pacific Hotel in front of 1,200 hairdressers. However, he was not able to pay Dickinson and her team for the job but said that if the programme was accepted, Venture would have rights to the (paying) business all across Canada.

As an entrepreneur, Dickinson viewed this as a golden opportunity to prove they could succeed, which could then lead to a lucrative national deal. It soon dawned on the three partners at Venture they couldn’t afford to get themselves out to Vancouver, let alone stay at the Pan-Pacific Hotel. Her two partners just happened to be sailors who also had accumulated a large number of Aeroplan points. They devised a plan to stretch the truth and claim Dickinson was the wife of one and the sister of the other, which would allow them to fly out to the Pacific coast free of charge.

Additionally, Dickinson’s two partners had a friend on Vancouver Island who owned a boat in a small town called Maple Bay. He offered free use of the boat and so the plan was that the three partners would travel in it to the mainland.

After landing on the island, the trio approached the vessel walking along the dock, but Dickinson somehow sensed her partners were becoming sheepish about something and not really saying much while walking slower and more tentatively, almost like a child who’s guilty of something and knows the truth is about to surface.

“I look ahead and I see the name of the boat is ‘Important Business’,” Dickinson states. “Now, why does that matter? I’ll tell you why it matters. They were always telling me they were away together on ‘important business.’ You can’t make this s**t up.”

The second secret the partners had kept from Dickinson was that they couldn’t afford the fee to dock in Vancouver’s harbour, so they eventually told her they’d be anchoring offshore. “Fine,” she said, no big deal.

The trio stayed up all night on the boat preparing for the big presentation in front of 1,200 hairdressers the following day. Upon exiting the shower, Dickinson went to use her hair dryer only to find there was no power. After an intense period of yelling and screaming with a frizzy, soaked head, the partners told her to simply put her hair in a little poof-ball on the top of her head and be done with it.

“I looked like Little Orphan Annie,” Dickinson chortles. Here she was, about ready to speak to a huge room of hairdressers, all the while having her own hair discombobulated in a knotted little poof-ball. Just when it seemed things couldn’t get any worse, she was informed that they’d be making the final part of the trip to shore on a small dinghy, because of course there was no money to dock the boat. Dickinson sat at the front of the tiny boat and by the time they’d reached shore she was soaked from head to toe, looking like a drowned poodle.

“We pull up to the dock where Bob is standing,” she explains. “He helps me up onto the dock and looks me up and down and says ‘we don’t have time to fix that.’”

Already late, Dickinson rushed to the hotel looking like she did with no time to change or try and make herself more presentable. But through all the immense adversity, she executed an outstanding presentation, doing an exceptional job of getting the message across. It was a resounding success!

“I realize the importance of knowing your content,” she emphasizes. “At the end of my presentation I must have had 1,199 hair dressers come up to me with their business cards saying in a sympathetic tone ‘honey, we can fix that,’” she says with a huge laugh.

From those early days of having virtually nothing, Dickinson now has a personal net worth of more than $80 million. Throughout the years she has won countless awards and has sat on the board of directors for a number of companies across Canada.

Advice to Others

As part of the new-age digital technology and how it ties in with marketing, she has some very poignant thoughts on how we go about doing business in this era. Dickinson encourages a business approach that blends life skills with business skills, and most importantly, relies on genuine face-to-face (or voice-to-voice) communications that allow you to tell your story.

“The art of storytelling is getting lost because we’re short-handing and texting our way through life,” Dickinson opines. “We aren’t communicating, we’re directing. Email is great for content, but not intent; it’s too open to interpretation by the person who’s reading it. So what happens? We put an email out there and then we’re surprised when somebody reacts to it the way they do because we certainly didn’t mean it the way they took it. Or we’re so busy worrying about how they’ll feel it takes us five hours to write the email to get them to do what we could have done if we’d just walked down the hall and told them directly.”

The overall message is that you stand up for who you are and that it’s okay to be who you are, asking in a good way how to get what you need without harming anyone in the process. Be the best you can be and you’ll be surprised at what can be achieved.

“I’ve crossed things off my list,” Dickinson gestures. “I won’t ever be a supermodel or a brain surgeon and there are lots of things I won’t ever be able to do because of my physical limitations, my age and my stage. Take that list away and the list of things that I can do is huge and that’s the same for everybody.”

In going from poverty to where she is today, Dickinson wasn’t ever afraid to fail – she was always afraid of regret. Never did she want to regret not having tried her best to succeed. It’s a lesson and motto for everyone to live by.